Written by Noah Lewis who was a member of Cannon's Jug Stompers. Some recordings of the song use the title Penitentiary Bound.

Many of the lyrics of Viola Lee Blues also occur in the similar song Joliet Bound, which is usually credited to Kansas Joe McCoy and which also appears to have been first recorded around 1929/30. It is possible that both songs derived from an earlier song or family of songs.

The Grateful Dead performed the song live between 1966 and 1970. Brief film of the Grateful Dead pplaying Viola Lee Blues can be seen in the 1968 movie Petulia and in the 1990's documentary Berkeley In The Sixties.